Old Town Winchester Travel Guide
Winchester
Visit Old Town Winchester
Popular places to visit
Museum of the Shenandoah Valley
You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.
Jim Barnett Park
Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.
Shenandoah Valley Discovery Museum
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.
Bright Box Theater
Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.
Old Court House Civil War Museum
You can study the exhibits at Old Court House Civil War Museum, a museum with a story of its own, during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
Staff was excellent- friendly, courteous. Helpful. Gym - small - but clean and most that you need. Pool - beautiful- on smaller side. Great bar vibe. Excellent location. This Wyndham so much better quality than the Wyndham we stayed at in Savannah, GA. Uno Pizzaria - connected to hotel - terrible ...
Reviewed on 2 May 2026
Spark by Hilton Winchester
Very nice, clean, great location. Breakfast could have been better. Would recommend.
Reviewed on 2 May 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Incredible front desk manager, who was unbelievably helpful when I checked in and made sure that I got everything I needed.
Reviewed on 2 May 2026
Microtel Inn & Suites by Wyndham Winchester
Super clean and modern, comfortable beds, staff very friendly and extremely helpful. Rooms are well equipped (fridge, coffee and tea) and standard hotel size, one space saving feature is no closet just a small rail will several coat hangers, and no room safe. One suggestion I would love to make is ...
Reviewed on 1 May 2026
La Quinta Inn & Suites by Wyndham Winchester
5 out of 5 stars Rooms were very clean. Beds were very comfortable. Best sleep I’ve ever had in a hotel. Staff were very helpful and kind. Everything within a 5 minute distance from hotel. Breakfast had a great selection of food including bagels, cereals, fruits, muffins, and eggs. Check in and check ...
Reviewed on 1 May 2026
Travelodge by Wyndham Winchester
Great check in; bed comfortable; could improve plug ins for cell phones and update lights. Sofa/furniture could becould be updated.
Reviewed on 3 May 2026
Other neighbourhoods around Old Town Winchester
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.
